


Continuing the Lesson

by thewinchesterlifestyle



Series: John's Lessons [4]
Category: Supernatural
Genre: Age Difference, Approval Starved Dean, Approval Starved Sam, Barebacking, Bondage, Bottom Castiel, Cheating, Cock & Ball Torture, Cock Cages, Conditioning, Dehumanization, Dildos, Dirty Talk, Exhibitionism, Extremely Dubious Consent, Forced Feminization, Gags, Humiliation, John Winchester Being an Asshole, John Winchester's A+ Parenting, Latex, Loss of Virginity, M/M, Multi, Naive Sam, Name Calling, Nipple Clamps, Nipple Play, Nipple Torture, Non-Consensual Body Modification, Objectification, Older John, Public Sex, Restraints, Rough Sex, Sex Club, Sex Toy Castiel, Sex Training, Sexual Grooming, Size Kink, Small Penis, Spitroasting, Teen Castiel, Teen Dean, Teen Sam, Top Dean, Top John, Top Sam, Underage - Freeform, Verbal Humiliation, Virgin Sam, Voyeurism, latex suit, teaching sex
Language: English
Status: Completed
Published: 2018-07-20
Updated: 2018-07-20
Packaged: 2019-06-13 16:11:20
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,188
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15368322
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: John was so grateful he’d stumbled across them fumbling around, trying to figure out how to have sex, because this opportunity would have never presented itself otherwise.





	Continuing the Lesson

**Author's Note:**

> Written for multiple prompts for various kinks/"lessons"/etc in this verse.
> 
>  
> 
> There are other prompts for continuations/lessons for this verse I didn't get to yet. I used the prompts/lessons/kinks that best fit in the next part.

He’d had to disguise Dean, to cover up the fact that his boy was underage, when he’d brought Dean along with him to the club. At the moment his son was tense but he had yet to take his focus from where Castiel was strapped down. John could _see_ where Dean was hard and straining against his pants. He knew his son was enjoying the sight in front of them especially considering how Dean kept shifting in his seat.

They had already been in the club for three hours and Castiel had seen constant use since the moment Dean had stepped away from strapping Castiel down. John had made _sure_ his son was the one to guide Castiel up, bend him over the stand and strap him down. It was very important that Dean start seeing Castiel in the way that John wanted him to.

It would be a waste otherwise.

“Isn’t that enough?”

Dean’s voice was low, worried and John frowned at him. “It _isn’t_ enough, son. She is learning how to be a good little slut. Maybe if you’d taken my first lesson seriously and actually used her cunt this wouldn’t be necessary but we can’t risk her failing to learn. Sometimes a lesson is learned if it is done hard, fast and happens repeatedly.”

He looked up and watched the two men roughly spit roasting his son’s boyfriend.

Castiel slim form was truly shone off in the skin tight black latex suit, legs splayed wide and cunt exposed for use. This time he’d put an o-ring gag in Castiel’s mouth. Learning to take it at both ends was just as important and this saved time.

It also looked very arousing.

“Maybe if you relieve some stress you’ll feel better.” John looked over at him, “Go use her cunt.”

Dean looked over at him, bit his bottom lip and slowly rose up to his feet. There had been several men who had come over, interested in what looked like a pretty twink, only for John to direct them to Castiel.

He watched Dean move up to the stand and wait until Castiel’s cunt was free. John stood and moved up close to watch. Castiel little hole gaped obscenely, come and lube dribbled from it, as John watched it clench on reflex.

While he watched Dean slowly moved up behind Castiel, stroking himself when John arched a brow, before pushing into Castiel’s sloppy hole. “Grip her hips and fuck that dirty cunt.”

Dean’s hands landed on Castiel’s hips, perfect hips for gripping when fucking, before he started moving.

It took less time for Dean to start enjoying himself than it had in the past. Soon enough John could _see_ that Dean had lost himself to the pleasure of fucking a warm and wet cunt. The thrusts came harder, faster and greedier as Dean’s fingers dug into Castiel’s hips.

Maybe the suit helped?

It certainly worked to dehumanize Castiel and maybe that was what was needed?

He could keep Castiel in the latex for Dean’s lessons and slowly start putting less and less on until Dean saw Castiel, no matter how he was presented, as a living sextoy.

That would make things so much easier. So much easier for him. If Dean saw Castiel in that way he certainly wouldn’t care if John borrowed him, if John collected Castiel at night and used the pretty teenager as he saw fit while his boys slept or played on their gaming system.

Castiel practically stayed at their house every weekend and having such easy access to that tempting little thing was a very lovely thought.

John walked back to his spot and watched his son pound into Castiel, fucking up against him harder and harder, before he slammed deep and came with a look of rapture on his face.

Reluctantly he watched Dean slip out and head back to him, glancing back and watching someone else slam inside Castiel with a grunt. The man using Castiel’s mouth finished and someone else took his place.

“Clean up.” He tossed the cloth he’d brought for Dean at his son and watched as he fumbled before tucking himself away. “See? It’s nothing more than a cunt in need of practice.” John watched the flush on Dean’s cheeks, “Did she feel good? All wet and open?”

Dean’s cheeks were darker and he mumbled something.

“Speak up.”

“… _yes_.”

“Yes, what?”

“Yes…she felt good…all wet and open.”

John nodded in approval. “Whenever you’re ready for another go I want you up there and using that cunt of hers…or her mouth. Whichever you want but the cunt always feels better in my opinion.”

Several hours later, Dean using Castiel twice more, John was plugging Castiel’s ruined cunt and guiding both of them out of the club.

Dean had gotten better. By the third time he was eagerly stepping up behind Castiel and slamming inside just like all of the others who had done the same. His son had fucked with enthusiasm and, to his pleasure, a noticeable lack of concern about the warm body he was pounding into.

Clearly the suit was helping with Dean’s own lessons.

Now John had something else in mind that would help to further push their lessons along. He took them back home, sent Dean off to bed and brought Castiel into his bedroom. John bent the still thoroughly bound teenager over his bed before reaching into the chest he’d filled with new purchases.

The penis gag he selected was thicker and longer. It swiftly replaced the o-ring gag, filling Castiel’s mouth and choking Castiel until he got used to it.

“Do you understand?” he asked as he unzipped his pants and with a lube slick palm started stroking himself, breathing hitching and cheeks flushing. “You’re a whore. A slut. A little sextoy that is only meant to give pleasure.”

He reached under and rubbed against the spot where Castiel’s little cock was caged within the suit. John took in Castiel’s balls, dark colored now, where the band remained. He moved his hand and checked the green castrating band.

It had only been that morning that he’d gotten a different band, a very specific band, for Castiel’s balls. He had no doubt that it wouldn’t be long before Castiel’s little balls dropped off. Castiel whimpered brokenly when he touched his little balls.

“You’re going to look really good when these come off.”

Castiel whimpered into his gag as John moved his hand, gripped his cock and pushed into that sloppy cunt. It felt so good. He was so grateful he’d stumbled across them fumbling around, trying to figure out how to fuck, because this opportunity would have _never_ presented itself otherwise and John had long learned to seize opportunities whenever they showed up.

He slammed deep, groaning his appreciation, before immediately starting to fuck. It was late and he wanted to get an early start on Castiel’s training.

John lost himself to the glorious feeling of pumping in and out of a slick, wet and ruined cunt. He gripped latex covered hips and pounded, the filthy sound of fucking through come and lube filled the room, as the mattress creaked with each hard thrust.

On the bed Castiel was moaning brokenly, ass clenching each time he fucked in, while John chased his pleasure. He could feel Castiel trying to push back but the position didn’t allow it.

This had really been the best idea he’d had in awhile. There was nothing like a young body to get lost in, a malleable mind to train for his pleasure, while also teaching Dean very valuable lessons. He’d only dreamed of getting this chance, got off on porn and stories but having it in real life was a million times better.

There couldn’t be any real kind of future with Castiel, Dean couldn’t possibly think that, but _this_ was something his son could certainly have and so could John.

He thrust harder and harder, his pleasure building, as his breathing picked up and John’s mouth fell open as he moaned. Castiel really felt amazing wrapped around him. That round, pert ass and the warm, slick hole were impossible to resist.

Castiel also made the most beautiful, sinful little sounds. Clearly Castiel had been born to be a bottom and John was only helping the teenager to realize that fact.

John fucked in one, two, three times and came with a groan of pleasure. His hips jerked forward a few times, chasing his lingering pleasure, before he pulled out. He turned and leaned down to pick up one of the long, thick dildos and started pushing it into the mess that was Castiel’s hole.

There were whimpers and whines, of course, but John focused on burying every inch into Castiel. He wiped the mess up with a discarded shirt and laid Castiel down on his back. The penis gag was replaced with a ball gag and thick bands were wrapped around Castiel’s legs until they were bound together.

Then he picked the whimpering teenager up and settled him in one of the lounge chairs in his bedroom that Mary had insisted on. After Castiel’s legs were propped up John turned away and went into the bathroom. After a quick shower he was slipping under his covers with a sigh of satisfaction.

* * *

“Dad I don’t think—”

“What, Dean? You don’t think Sam is ready?” he asked, knowing exactly what to say to get both of his sons to comply. “Do you think he’s a child? That he isn’t ready? That he isn’t ready to be a man?”

“That isn—”

“I am too!” Sam had a look of defiance on his face and John didn’t bother to hide the amusement. His youngest looked up at him, “Right, Dad? I’m not a little kid. I’m ready to become a man.”

John patted him, “Of course not, Sammy. I know you’re ready. You’re ready to become a man. I know you can do this.”

Castiel was covered in latex to the neck, gagged and laid out over the bed. He needed Dean to see Castiel the right way, to see him as a sextoy, otherwise Dean wasn’t going to take to his lessons like John needed and wanted him to.

“Now do you remember what I said to you about her?”

Sam nodded, eager to please since they had lost Mary and desperate to show he was just as good as Dean. “Of course, Dad. You said she’s a toy and that her purpose is to give pleasure to whoever is using her. Dean was using her wrong.”

It sounded like he was answering a test question.

“Exactly. Good boy.”

Sam seemed to swell with the praise.

“Now…do you know what to do?” he asked but already knowing the answer. John had caught Sam watching some of Dean’s porn on the laptop and he knew his son was curious about sex, interested in it. He had made Sam watch Dean using Castiel just to makes sure he would be ready. Sam nodded in response to his question. “Good. Now, remember, this is a learning experience. Just make sure you enjoy yourself.”

He gripped Dean’s shoulder and held his son in place as Sam went through all of the instructions and guidelines he’d given him earlier when he had first brought Castiel into the room.

Sam’s body was quick to respond, hormones already eagerly surging inside of him, as he stroked himself with a look of concentration. He stepped up and, after pausing, pressed his fingers into Castiel’s come wet cunt.

His youngest had already watched Dean fuck Castiel with John’s instructions guiding him and Sam had always been a fast learner.

Sam fingered Castiel for a bit before pulling his fingers back and moving to straddle Castiel’s thighs. It wasn’t coordinated and was obvious that Sam was trying to mimic what he’d seen.

Slowly Sam pushed in, a gasp escaping his parted lips, before he started moving in messy jerks of his hips.

“You can go as hard and rough as you want, Sammy. She’s purely a wet hole to use.”

Dean jerked next to him.

“Stroke yourself, Dean.” John snapped the order out and watched as Dean complied, pulling his semi-hard cock out and stroking it after adding some lube to slick his palm. “Watch Sam use _your_ sextoy. See, Dean? That’s what she’s for.”

Something could be said for Sam’s enthusiasm and eagerness as he fucked Castiel. John could see him figuring out what worked, what he enjoyed and changing until his mouth was falling open. Pleasure had Sam’s cheeks flushing as he jerked and his pace stuttered until he was groaning.

“That…that wasn’t as long as Dean…” he sounded disappointed but his soft cock pulled out and he climbed off Castiel without a backwards glance.

“You’re younger, Sam. You’ll get better.” John slanted a glance over at Dean before looking back at Sam. “ _Anytime_ you want to practice using her just tell her to bend over and you can take her right there. She’s purely for pleasure and our use, Sammy. Don’t feel bad for instructing her so you can practice.”

Sam didn’t seem to have any problem with that. “Ok, Dad.” He bit his lip, “Is this…is this normal? Part of becoming a man?”

“Of course it is, Sam. I wouldn’t lie to you but not everyone understands so you can’t tell anyone. This is a family secret, Sammy. Do you understand?”

“Of course! I’m not going to say anything.”

“Good job. I’m so proud of you. Losing your virginity and becoming a man.” Sam seemed pleased, “Go clean up and enjoy your break.” He ruffled Sam’s hair, “And remember…any time you want to practice just order her to bend over or lay down for you.”

Sam nodded and darted out of the room.

“Did you see that? Even _little_ _Sammy_ understands that she’s nothing more than a toy, Dean. All those men who used her in the club know she’s a toy for pleasure. Why can’t you understand?”

Dean looked ashamed, cheeks flushed and eyes unable to meet his.

“At least one of my sons isn’t going to fail me. At least I can have _that_.” He could see something steel itself in Dean’s eyes, the way his son’s chin came up stubbornly, as he yanked his pants and underwear off the rest of the way. His hard cock hung there as he climbed upon to the bed and, without an ounce of hesitation, fucked right into Castiel’s cunt.

Dean’s hands braced on the mattress on either side of Castiel as he moved, roughly snapping his hips forward, as he fucked himself in and out of Castiel. The determination slowly faded in the face of pleasure and enjoyment as Dean’s movements became more natural.

“That’s it, son. That’s right. Use her. She’s nothing but a slut…a pretty whore with a set of holes for our pleasure.”

Dean was moaning as he moved, harder and faster, as Castiel whined and moaned underneath him. He could see the flush to Castiel’s cheeks as he moaned into his gag.

“She _loves_ being used. Can’t you hear her?”

He watched his son pound into Castiel, getting lost to the pleasure of a good fuck, until Dean slammed in and came with a groan of bliss. “Fuck.”

“Exactly. She feels real good, doesn’t she?”

“Yeah…she does.” Dean’s voice was rough as he pulled out and glanced over at John before reaching for the thick plug he’d been using. He lubed it up and pushed it against Castiel’s puffy hole until it popped past the ring of muscle to sink inside.

“That was twice, Dean. You still have at least two more times to use her today and I expect you to do that.” John watched Dean climb off the bed, cleaning himself up, before pulling his clothing back on. “You _can_ use her more than that. In fact I encourage you to. Toys or your dick, whichever you want but _use her_. That’s what she was born for.”

Dean nodded, eyes not quite meeting his.

“You’re free. I know you said something about hanging out with your friends.”

Then Dean was gone and John was left, once again, with Castiel. He reached out and hauled Castiel towards the edge of the bed.

“All three of us are going to help you become what you were always meant to be. I’m sure you’re going to be a good girl for us.” John watched the way Castiel whined as his ass pressed to the bed, pushing the plug deeper and pressing against his bound balls. “You’re going to be a proper whore in no time. You’re going to know how good it feels to give others pleasure and let them use your body.”

He reached into the chest to grab a few nipple clamps with weights on them. John attached one to the right nipple and another to the left. Castiel jerked, a muffled whimper escaping, as John nodded.

“There we go.” He would add weights to Castiel’s balls but, since he was doing something else there, it wouldn’t be as effective. “You’ll warm my dick with your mouth while I work in my office.”

Castiel stumbled after him as John led the way and guided the teenager underneath his desk. The gag was placed to the side and, once his cock was free, Castiel was soon taking him into his hot little mouth.

“That’s good, whore. Very good. Keep sucking and licking.”

John moaned softly as Castiel immediately started sucking on him. There was _nothing_ like a warm, wet mouth on his cock while he was working. At this rate Castiel would be a pro at following every last one of John’s orders and every possible sex position.

Anyone who enjoyed Castiel in the future would have John to thank for how good Castiel was with his mouth and body.

He was grateful that Castiel’s parents were on a trip while school was on break. It would give him plenty of time to work on Castiel, twenty-four seven, while also helping Dean overcome his hang ups about using Castiel.

It wouldn’t be a success until Dean ordered Castiel into position without prompting and took his pleasure without thinking about Castiel’s though it was more than obvious the little whore enjoyed it rough, enjoyed being taken over and over.

John could hear Castiel moaning, feel Castiel starting to eagerly push back into the cock fucking her hole. It would be harder if Castiel wasn’t so easily susceptible to condition but John had done his research and he knew exactly what to do. He knew how to word things, the importance of repetition, and not having conflicting interactions.

It was part of the reason he’d had Sam use Castiel. Now he could keep Castiel naked or wrapped in latex and free to use even when Sam was in the house without worry of anything going wrong.

This was the first break his boys had that he was going to actually be able to relax.

**Author's Note:**

> Like I had mentioned...there were other prompts and I wove a few kinks/requests from newer prompts into this one. There are still others but they didn't fit at this point of time. A lot of you wanted me to toss Sam in there so this one was the first step in that very popular request along with multiple requests about poor Cas's balls.
> 
> I have noticed this is one of my more popular verses so I thought I'd go ahead and bang this one out for you all after the nice response I received for "Lesson Reinforcement".
> 
> I know this is one of my more popular verses so I'm hoping you enjoyed this one. Please leave a comment and let me know what you thought. Remember comments are motivation for continuing to write and post fanfics!  
> 


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